Triethylamine → 4-Formyl-4'-(trifluoromethyl)benzanilide

HRID 480950Notes

Reaction equation

HRID 480950 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)=[O:20]>CN(C)C1C=CN=CC=1>[CH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=2)=[O:26])=[CH:23][CH:22]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 187663494-Formyl-4'-(trifluoromethyl)benzanilideYield 71%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the same manner as that described in Example 2(1), a reaction was carried out using commercially available 4-(trifluoromethyl)aniline (446 mg, 2.8 mmol), triethylamine (0.6 ml, 4.4 mmol), 4-formylbenzoyl chloride (700 mg, 4.2 mmol) and 4-(dimethylamino)pyridine (a catalytic amount) and the reaction mixture was treated according to a similar procedure to that described in Example 2(1) to afford 4-formyl-4′-(trifluoromethyl)benzanilide (577 mg, yield 71%) as a white solid which was recrystallized from ethyl acetate-hexane to give white fluffy crystals.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-b8b357437ad846aba52a765a9441270f
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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